CN101287724A - 经吡咯取代的2-吲哚酮的固态盐形式 - Google Patents
经吡咯取代的2-吲哚酮的固态盐形式 Download PDFInfo
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Abstract
Description
相对离子 | 结晶的盐 | 熔点(℃) | 80%RH时的水% | HPLC纯度* | 异构体%* |
无(自由碱) | NA | 257 | ~1% | 97.8 | 0.63 |
盐酸盐 | 是 | 96 | ~20% | 97.7 | 2.29 |
反丁烯二酸盐 | 是 | NA | ~9% | 97.3 | 1.96 |
柠檬酸盐 | 是 | 181 | ~3.8% | 98.2 | 1.38 |
磷酸盐 | 是 | 288 | ~1% | ||
抗坏血酸盐 | 是 | 245 | ~6.5% |
溶剂 | 化合物I游离碱的溶解度(同质多晶形体形式A)(mg/mL) | 化合物I磷酸盐的溶解度(mg/mL)d | |
1 | 缓冲液(pH=2)a | 3.11 | 5.9-7.4 |
2 | 缓冲液(pH=5)b | 0.005 | |
3 | 水 | NAc | ~0.29e(一些颗粒粘在瓶壁上,没有溶解) |
4 | 甲醇 | 0.21-0.31 | ~0.14 |
5 | THF | 0.32-0.4 | <<<0.19 |
6 | 乙腈 | <<0.08 | <<<0.13 |
7 | 丙酮 | <<0.16 | <<<0.2 |
被指定给PXRD图的名称 | 有机溶剂 | PXRD结晶度 | 显微观察 | TGAwt%损失 | DSC的热事件(℃)b | 固体颜色 | 自由流动(Y=可;N=不) |
形式I | 水+ACN | 高 | 不规则 | 0.3 | 296 | 橙色 | Y |
形式II | EtOH | 不良 | 聚集e | 2.5 | 81c,226,293 | 黄色 | N(粘) |
形式I | MeOH | 高 | 不规则 | 1.7 | 298 | 橙红色 | Y |
形式III | 丙酮 | 中等 | 聚集e | 2.5 | 88c,155,222,228,286 | 黄色 | N(粘) |
形式IV | 乙腈(ACN) | 高 | 聚集e | 2.9 | 97c,142,156,172,227,230,281 | 黄色 | N(粘) |
形式V | THF | 高 | 聚集e | 2.5 | 82c,161,175,227,292 | 黄色 | N(粘) |
NDf | 乙酸乙酯 | 不良 | 细颗粒 | 4.7 | 98c,196,222 | 淡橙色 | N(粘) |
NDf | 己烷 | 不良 | 聚集e | 淡橙色 | N(粘) | ||
形式VIg | CH2Cl2 | 中等 | 板状+等分+细 | 3.3 | 123d,164,228,296 | 橙红色 | Y |
NDf | IPA | 不良 | 聚集e | 1.9 | 76c,222,229,296 | 黄色 | N(粘) |
被指定给PXRD图的名称 | 有机溶剂(静置时间) | PXRD结晶度 | 显微观察 | wt%损失 a | DSC的热事件(℃)b | 固体颜色 | 自由流动(Y=可;N=不) |
形式I | 水+ACN | 高 | 不规则 | 0.3 | 296 | 橙色 | Y |
形式I | 乙酸乙酯(过夜) | 高 | 片状 | 橙红色 | Y | ||
形式VIIg | 己烷(过夜) | 中等 | 板状 | 2.4 | 124c,228,295 | 橙红色 | N |
形式I | IPA(过夜) | 高 | 等分(25μm)+细 | 0.4 | 297 | 橙红色 | Y |
形式I | CH2Cl2(过夜) | 高 | 等分(25μm)+细 | 0.6 | 293 | 橙红色 | Y |
形式I | EtOH(3天) | 高 | 聚集e | 橙红色d | Y | ||
形式I | 丙酮(3天) | 高 | 板状 | 橙红色e | Y | ||
形式VIIg | 乙腈(3天) | 中等 | 针状 | 4.9 | 153c,229,231,239,291 | 橙红色e | N |
形式I | THF(3天) | 高 | 矛状头 | 0.3 | 295 | 淡橙色f | N |
形式I | MeOH(过夜) | 高 | 橙红色 | Y | |||
形式I | MEK(过夜) | 高 | 棒状 | 0.6 | 297 | 橙色 | N |
形式I | 二恶烷 | 高 | 板状 | 295 | 橙色 | N |
被指定给PXRD图的名称 | 晶体产生方法 | PXRD结晶度 | DSC的热事件(℃)b | 固体颜色 |
形式IX | ACN溶剂化物的去溶剂化 | 不良 | 74,174,229231,239,291 | 橙色 |
形式X | 己烷溶剂化物的去溶剂化 | 中等 | 橙色 |
患者编号 | 肿瘤级别 | 是否存在c-kit ITD突变 | 血浆化合物I磷酸盐剂量后(ng/mL) | P-KIT降低剂量后a | P-ERK1/2减低剂量后 |
1 | III | 是 | 81.0 | 是 | 否 |
2 | III | 是 | 33.2 | 是 | 否 |
3 | II | 是 | 83.5 | NE | 是 |
4 | III | 是 | 98.0 | 是 | 是 |
5 | III | 是 | 116.0 | 是 | 是 |
6 | III | 否 | 121.0 | 是 | 是 |
7 | III | 否 | 186.0 | NE | NE |
8 | III | 否 | 0.3 | 是 | 否 |
9 | II | 否 | 103.0 | NE | NE |
10 | II | 否 | 111.0 | 否 | 是 |
11 | II | 否 | 158.0 | 否 | 是 |
12 | II | 否 | 65.3 | 是 | 是 |
13 | II | 否 | 95.4 | 否 | 否 |
14 | III | 否 | 119.0 | 是 | NE |
Claims (17)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310478975.0A CN103601720B (zh) | 2005-09-19 | 2006-09-08 | 经吡咯取代的2-吲哚酮的固态盐形式 |
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Application Number | Priority Date | Filing Date | Title |
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US71858605P | 2005-09-19 | 2005-09-19 | |
US60/718,586 | 2005-09-19 | ||
PCT/IB2006/002506 WO2007034272A1 (en) | 2005-09-19 | 2006-09-08 | Solid salt forms of a pyrrole substituted 2-indolinone |
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CN201310478975.0A Division CN103601720B (zh) | 2005-09-19 | 2006-09-08 | 经吡咯取代的2-吲哚酮的固态盐形式 |
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CN101287724A true CN101287724A (zh) | 2008-10-15 |
CN101287724B CN101287724B (zh) | 2013-11-06 |
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CN2006800345053A Active CN101287724B (zh) | 2005-09-19 | 2006-09-08 | 经吡咯取代的2-吲哚酮的固态盐形式 |
CN201310478975.0A Active CN103601720B (zh) | 2005-09-19 | 2006-09-08 | 经吡咯取代的2-吲哚酮的固态盐形式 |
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US (3) | US20080275101A1 (zh) |
EP (2) | EP1928858B1 (zh) |
JP (2) | JP4519114B2 (zh) |
KR (1) | KR101050906B1 (zh) |
CN (2) | CN101287724B (zh) |
AR (1) | AR056521A1 (zh) |
AU (1) | AU2006293644B2 (zh) |
BR (1) | BRPI0616374B8 (zh) |
CA (1) | CA2621569C (zh) |
CY (1) | CY1109326T1 (zh) |
DE (1) | DE602006008015D1 (zh) |
DK (1) | DK1928858T3 (zh) |
ES (1) | ES2328407T3 (zh) |
HK (1) | HK1125101A1 (zh) |
IL (1) | IL189590A0 (zh) |
MX (1) | MX2008002415A (zh) |
NO (1) | NO20080866L (zh) |
NZ (1) | NZ566033A (zh) |
PL (1) | PL1928858T3 (zh) |
PT (1) | PT1928858E (zh) |
RU (1) | RU2399619C2 (zh) |
SI (1) | SI1928858T1 (zh) |
TW (1) | TWI310766B (zh) |
WO (1) | WO2007034272A1 (zh) |
ZA (1) | ZA200801431B (zh) |
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Publication number | Priority date | Publication date | Assignee | Title |
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SI1928858T1 (sl) | 2005-09-19 | 2009-10-31 | Pfizer Prod Inc | Trde solne oblike s pirolom substituiranega 2-indolinona |
US20100189791A1 (en) | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline malate formulation |
EP2545034A1 (en) | 2010-03-10 | 2013-01-16 | Synthon B.V. | A process for amidation of pyrrole carboxylate compounds |
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US6574293B1 (en) | 1998-10-28 | 2003-06-03 | Ericsson Inc. | Receivers and methods for reducing interference in radio communications |
US20020010203A1 (en) * | 1999-12-22 | 2002-01-24 | Ken Lipson | Methods of modulating c-kit tyrosine protein kinase function with indolinone compounds |
NZ520640A (en) * | 2000-02-15 | 2005-04-29 | Upjohn Co | Pyrrole substituted 2-indolinone protein kinase inhibitors |
US6797725B2 (en) * | 2001-04-09 | 2004-09-28 | Sugen, Inc. | Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
PT3168218T (pt) | 2001-08-15 | 2019-01-11 | Pharmacia & Upjohn Co Llc | Um cristal compreendendo um sal de ácido l-málico de n-[2- (dietilamino)etil]-5-[(5-fluoro-1,2-dihidro-2-oxo-3h-indol- 3-ilideno)metil]-2,4-dimetil-1h-pirrol-3-carboxamida para utilização como um medicamento |
US7119209B2 (en) * | 2002-02-15 | 2006-10-10 | Pharmacia & Upjohn Company | Process for preparing indolinone derivatives |
US7452913B2 (en) * | 2003-02-24 | 2008-11-18 | Pharmacia & Upjohn Company | Polymorphs of pyrrole substituted 2-indolinone protein kinase inhibitors |
US20040209937A1 (en) * | 2003-02-24 | 2004-10-21 | Sugen, Inc. | Treatment of excessive osteolysis with indolinone compounds |
US20060009510A1 (en) * | 2004-07-09 | 2006-01-12 | Pharmacia & Upjohn Company Llc | Method of synthesizing indolinone compounds |
SI1928858T1 (sl) | 2005-09-19 | 2009-10-31 | Pfizer Prod Inc | Trde solne oblike s pirolom substituiranega 2-indolinona |
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